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10 Festive Events to Celebrate Fall in Southwest Florida

With temps dropping and seasonal residents returning to town, there's no shortage of u-picks, festivals and spooky events to fill your calendar.

BY October 9, 2020

In many other places, you can feel that fall is upon you with the arrival of the cool air and the changing leaves. In our regionthe start of the season is marked by the prevalence of events.  

This year is no exception. Though many of the bigger soirees are canceled and we’re still urged to be careful, there are fun opportunities to get out and enjoy the picture-perfect days and nightsWith many annual events returning, and new ways to gather cropping up, October arrives with a slate of festivals and shows 

So, grab your friends and family and mark your calendars for these dates that celebrate the best of life in paradise 


  • Farmer Mike’s U-Pick welcomes you to the 6th Annual Fall Festival, with family-friendly and haunted corn mazes every Friday through Sunday throughout the month of October. Expect food vendors, bounce houses (sanitized regularly), crafts and u-pick pumpkins. Ticket prices vary. 


  • Salty Sam’s Pirate Cruise does it up with its popular Rocky Horror Picture Show Cruise, which includes rum tastings, trivia and costume contests on Friday Oct. 16 from 7:30 to 9 p.m. Check the schedule for a kid-friendly party and the restaurant’s Halloween masquerade ball. $25 per ticket. 


  • Edison and Ford Winter Estates welcomes guests to enjoy the first of those cool fall breezes after-hours during its Autumn Nights at Edison Ford Oct. 16 from 6 to 9 p.m. $20 per ticket; $15 for members. 


  • The Naples Players airs Little Shop of Horrors Oct. 20-21 at 8 p.m. for its monthly Drive-in Movie Nights$45 per car for general public; $20 for members. (Psst… Gulfshore Life readers get the $20 price when you use code ‘GSL20’ at checkout.) 


  • Artichoke and Company kicks off its fall celebration with great food, live music and games at Oktoberfest on Oct. 17, from 4 to 9 p.m. Pick up pumpkins muffins, mummy pizza, sweet potato bites and candy apples to take home from the Kids Halloween Cooking Demo on Oct24 from 10 a.m. to 12 p.m. Cooking demonstration, ages 5 to 10, $50 per child; costumes encouraged. 


  • Mercato hosts its annual Hallowine costume wine walk returns Oct. 28, from 6 to 9 p.m., as the Naples Gulfshore Rotary Club’s largest fundraiser. Don your costume to strut around the shopping center as you sample fine wine and bites. $60 per ticket or $200 for our; $75 per ticket at the door. 


  • Florida Repertory Theatre’s Stage@Home series closes its limited fall run with a Ghostlight Halloween Special—including panelists sharing ghostly tales and other spooky topicsOct. 30 at 3:30 p.m. $20 per ticket. 


  • Golisano Children’s Museum of Naples hosts a Trunk or Treat Car Parade. Roll down your windows and trick or treat as you drive through the site on Oct. 30 from 6 to 8 p.m. Decorate your car for a chance to win a C’mon membership.  $15 per car. 


  • Millennial Brewing Company offers a full night of spooky fun on Oct. 30 with its Trunk or Treat from 7 to 10 p.m., when kids can trick-or-treat from decorated car trunks, while the party continues for the grown-ups from 6 p.m. to 1 a.m., with themed music, beers and cocktails, and a costume contest during the Halloween BashFree admission; $3 for a tailgate spot.


  • Fifth Avenue South invites you to join them for a virtual Halloween Spooktacular. Follow 5th Avenue South on social media for further event updates regarding a special Instagram & FB LIVE Virtual Halloween Showcase on October 31st, 4:30pm to 7:30pm.


For a seasonal sip, swing by these local brewers for a variety of fall-themed coffee or tea beverages. Try the Maple Spice Latte, Pumpkin Pie Latte, Autumn Harvest Chai, Apple Fritter Chai or Felix Fall-icis (Liquid Luck) Latte from Narrative Coffee Roasters. Enjoy a fallblend Chagaccino, Golden Latte or classic Pumpkin Spice Latte from Kunjani Craft Coffee & Gallery. Or, grab a Pumpkin Spice Oat Milk Latte from Shift Coffee Bar (trike schedule varies). 


Photo courtesy Getty Images.

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